Tetrahedron p. 13961 - 13970 (1996)
Update date:2022-08-02
Topics:
Omote, Masaaki
Ando, Akira
Takagi, Toshiyuki
Koyama, Mayumi
Kumadaki, Itsumaro
Benzyl 3,5-dimethyl-2-pyrrolecarboxylate (1) was converted to 4-(2,2,2-trifluoro-1-hydroxyethyl) derivative (2) on treatment with trifluoroacetaldehyde ethyl hemiacetal in the presence of zinc chloride. After protection of the hydroxyl group with a methyl group, 2 was converted to benzyl 4-methyl-3-(2,2,2-trifluoro-1-methoxyethyl)-2-pyrrolecarboxylate (9) and benzyl 5-acetoxymethyl-3-methyl-4-(2,2,2-trifluoro-1-methoxyethyl)-2-pyrrolec arboxylate (10). Both esters were condensed to dipyrylmethane compound 11, which was debenzylated, decarboxylated, and condensed with a bottom half of the porphyrin to give hexafluorohematoporphyrin derivative 14, potentially useful for photodynamic therapy of cancer.
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